Most elderly people choose to age in place, making neighborhood environments essential factors affecting their health status. The policies, economic status, and housing conditions of old neighborhoods have led many elderly people to live in skipped-generation households (SGHs), where they have gradually weakened physical functions and are responsible for raising grandchildren; this puts their health in a more fragile state than that of the average elderly person. Practical experience has shown that when faced with complex environmental renovation problems in old communities, many cases often adopt a one-step treatment strategy; however, many scholars have questioned the sustainability of such unsystematically evaluated renovation projects. Therefore, it is often valuable to explore the root causes of these old neighborhood problems and conduct targeted transformations and upgrades according to the interactive relationship between various influencing factors. This study attempted to establish a novel evaluation system to benefit the health of elderly families in old neighborhoods and develop an understanding of the impact relationship among the indicators, while avoiding any form of waste when collecting responses in regard to the future transformation of old neighborhoods. A questionnaire survey was conducted on the elderly in the Guangzhou Che Bei neighborhood in China, and by applying the rough set theory of the decision-making trial and evaluation laboratory model, we established a preliminary evaluation system, obtained key environmental factors affecting the health of elderly people living in SGHs, and clarified their mutual relationships. Finally, on this basis, we proposed corresponding neighborhood renewal suggestions. The results of this study provide a theoretical basis for future research, and our research model can be applied to similar aging research in the future.